How many times do you have to have before it doesn't hurt?

I've tried for about a week w/my fiance. He couldn't even put it in a little without immense pain on my end. By the time he did, slowly, it hurt like crazy and I bled a lot. Anyway eventually he was able to actually do but only if we use a lot of lubricant and only if he goes a little slow and only in the missionary position and it still hurts me then too. We tried other positions but there is just no way, he's just too big. How many times will we have to try before we can become normal?